Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester | 308806-97-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester
• 英文别名: [(3R,4R,5S)-4-azido-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl] trifluoromethanesulfonate
• CAS: 308806-97-5
• 化学式: C₁₀H₁₂F₃N₃O₇S
• 分子量: 375.282
• InChiKey: NYTOZRFYPNZNKW-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  甲醇 、 Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester 在 盐酸 作用下， 生成 3(R)-Azido-4(S)-hydroxy-5(R)-hydroxymethyl-tetrahydro-furan-2(S)-carboxylic acid methyl ester
  参考文献：
  名称：

  3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?

  摘要：

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00205-0
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 吡啶 、 sodium azide 、 camphor-10-sulfonic acid 、 溴 、 barium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester
  参考文献：
  名称：

  3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?

  摘要：

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00205-0
• 作为试剂：
  描述：

  乙酰氯 、 Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester 、 碳酸氢钠 在 氮气 、 Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester 、 silica 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以v/v) as the eluent afforded (59) as a white solid (73 mg, 68%)的产率得到3(R)-Azido-4(S)-hydroxy-5(R)-hydroxymethyl-tetrahydro-furan-2(S)-carboxylic acid methyl ester
  参考文献：
  名称：

  Cysteine protease inhibitors

  摘要：

  Cathepsin S是一种高活性的半胱氨酸蛋白酶，属于木瓜蛋白酶超家族。它主要存在于淋巴结、脾脏和巨噬细胞中，这种有限的出现提示了这种酶在退行性疾病的发病机制中可能的参与。本发明涉及新型蛋白酶抑制剂，特别是木瓜蛋白酶超家族的半胱氨酸蛋白酶抑制剂，更特别地是Cathepsin S的抑制剂。这些抑制剂是具有特征性非氢取代基R5的呋喃酮衍生物，它们对家族中的其他成员具有选择性，特别是对其他Cathepsin家族成员如L和K具有选择性。

  公开号：

  US20050020588A1

文献信息

• Furanone derivatives as inhibitors of Cathepsin S
  申请人：Medivir UK Ltd

  公开号：EP1413580A1

  公开（公告）日：2004-04-28

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.

  Cathepsin S 是一种属于木瓜蛋白酶超家族的高活性半胱氨酸蛋白酶。它主要存在于淋巴结、脾脏和巨噬细胞中，这种有限的存在表明这种酶可能参与了变性疾病的发病机制。本发明涉及新型蛋白酶抑制剂，特别是木瓜蛋白酶超家族半胱氨酸蛋白酶的抑制剂，尤其是 Cathepsin S。它们对该家族的其他成员具有选择性，特别是对酪蛋白酶家族的其他成员如 L 和 K 具有选择性。
• FURANONE DERIVATIVES AS INHIBITORS OF CATHEPSIN S
  申请人：Medivir UK Ltd

  公开号：EP1178986B1

  公开（公告）日：2004-02-25
• 3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?
  作者：Mark P Watterson、Lea Pickering、Martin D Smith、Sarah J Hudson、Paul R Marsh、Jacqueline E Mordaunt、David J Watkin、Christopher J Newman、George W.J Fleet

  DOI：10.1016/s0957-4166(99)00205-0

  日期：1999.5

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Cysteine protease inhibitors
  申请人：——

  公开号：US20030203900A1

  公开（公告）日：2003-10-30

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.

  Cathepsin S是一种高活性的半胱氨酸蛋白酶，属于木瓜蛋白酶超家族。它主要存在于淋巴结、脾脏和巨噬细胞中，这种有限的出现表明该酶可能参与退行性疾病的发病机制。本发明涉及新型蛋白酶抑制剂，特别是木瓜蛋白酶超家族的半胱氨酸蛋白酶抑制剂，尤其是Cathepsin S。这些抑制剂是具有特征性非氢取代基R5的呋喃酮衍生物式（II）。它们对家族中的其他成员具有选择性，特别是对L和K等Cathepsin家族的其他成员表现出选择性。